Hart’s Josh Herman (24) and the rest of the boys basketball team celebrates a win in the 2005 CIF-Southern Section Division IAA semifinals.

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Mike Herrington still remembers even the minor details of that mid-December evening in 2003.

Hart High football captured its eighth CIF title and its sixth with Herrington as head coach.

It certainly wasn’t Herrington’s first championship experience, but this one was special for one important reason — it wasn’t supposed to happen.

“I can remember running off the field at halftime with the lead, running off with my brother Rick and saying, ‘Can you believe this? Can we keep this up?’” Herrington says.

They did keep it up, and went on to shock heavily favored Mission Viejo 25-7 for the CIF-Southern Section Division II title. Mission Viejo had won 41 straight games leading up to the matchup and had beaten Hart 10-6 in the previous year’s title game.

In 2005, Hart upset Mission Viejo again, this time in the CIF-Southern Section Division II semifinals. The 24-12 win ended a 26-game win streak by the Diablos, who were then ranked No. 2 in the nation by USA Today.

Upsets can be the most elating or heartbreaking occurrences in sports. History, analysis and statistics can tell us who is supposed to win and who is supposed to lose.

But sometimes, it’s all wrong. The underdog somehow pulls off the unthinkable.

“I would much rather be the underdog,” says Saugus girls soccer head coach Natalie Helgeson. “The stress isn’t there and you don’t have anything to prove.”

Helgeson, a former soccer player at University of the Pacific, recalls her team upsetting Brigham Young University, which was ranked No. 22 in the National Soccer Coaches Association of America at the time.

The 3-2 victory on October 31, 1997, was the school’s first-ever win over a ranked team.

In the case of upsets, the team that wins is often billed as less talented or less skilled coming into the matchup.

So how does a team like Hart’s 2005 boys basketball squad put together a run to a CIF division title game after finishing just third in the Foothill League?

“I think we went into it with a nothing-to-lose kind of attitude,” says Ryan Wolfe, who played on the 2005 Hart team. “Not to downplay who we were, but no one really expected us to do anything in the tournament.”

The Indians came into the CIF-Southern Section Division IAA playoffs that year with a 14-12 record and had to play a wild-card game just to earn a spot in the bracket.

Once the playoffs began, Hart came with a renewed sense of urgency.

“I can still remember every day in practice that the intensity level was so high, we almost started getting in fights with each other,” Wolfe says.

And the intensity picked up as the Hart moved deeper and deeper into the playoffs. Five straight teams fell victim to the overachieving Indians during the run, eventually culminating in a 53-41 win over Diamond Bar in the semifinal game.

“When that clock was winding down, all of us coaches, we looked at each other kind of in a little bit of disbelief like, ‘What the heck? We’re going to The Pond,’” says head Hart boys basketball coach Tom Kelly in reference to the Arrowhead Pond of Anaheim which is now known as the Honda Center.

That was the site of the championship game, where Hart lost 60-45 to Etiwanda.

For every story like Hart’s, there is an equally surprising result for the opposite reason. The utter joy felt by those involved in an upset win can be just as strong as the disappointment and letdown from a loss.

That was especially true with the 2011 Saugus softball team. After winning the Foothill League title and earning a favorable matchup at home in the first round of the playoffs, Saugus was turned away 8-0 by Canyon of Anaheim.

It was an unexpected ending to a promising season.

“It’s a frustrating feeling,” says Saugus softball coach Julie Watson. “You know your potential and what could have happened and the talent on the team.”

The loss spelled the end of several players’ high school careers.

“The girls were more sad the journey had ended because we had so many seniors, and frustrating at the same time,” Watson says. “You wish you would have done better, but in sports, it happens.”

Upsets stem from expectations. If those expectations are too high, the upset factor can swing the other way and bring about a painful result.

The same thing that will leave one side scratching its head wondering what went wrong will leave the other side in astonishment over what it has accomplished.

In the rare occasions when the long shot finally does win, it can provide some of the most memorable and exciting moments in sports.